Thionyl Chloride → 4-(4-Trifluoromethylphenyl)benzylchloride

HRID 1672624Notes

Reaction equation

HRID 1672624 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:18])([F:17])[F:1])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22015014(4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-yl)methanol

Product 1

HCID 114599214-(4-Trifluoromethylphenyl)benzylchlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 5.0 g (19.82 mmol) of (4′-trifluoromethylbiphenyl-4-yl)methanol from Example 22A in 40 ml of chloroform is mixed with 2.89 ml (39.65 mmol) of thionyl chloride dissolved in 10 ml of chloroform, and the mixture is stirred at room temperature for 12 hours. After reaction is complete, the reaction mixture is concentrated to dryness, and the residue is taken up ethyl acetate and washed with saturated sodium carbonate solution. The organic phase is subsequently separated off, dried over sodium sulfate and concentrated after filtration. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). 5.26 g (19.43 mmol, 98% yield) of a colorless solid are obtained.

Workup

  1. customAfter reaction
  2. concentrationthe reaction mixture is concentrated to dryness
  3. washwashed with saturated sodium carbonate solution
  4. customThe organic phase is subsequently separated off
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. filtrationafter filtration
  8. customThe crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-a40ec2f94b984c8383f1f61fe4e0f386
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

Loading…